Lewis Acid Mediated Synthesis of 2-Alkenenitriles Using C,N-Bis(trimethylsilyl)ketenimine and Carbonyl Compounds
- 1 February 1983
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 56 (2) , 528-532
- https://doi.org/10.1246/bcsj.56.528
Abstract
2-Substituted 2-alkenenitriles are obtained in the condensation reaction of carbonyl compounds with C,N-bis(trimethylsilyl)ketenimine in the presence of Lewis acid. The combination of tris(trimethylsilyl)ketenimine and aldehydes results in the high E-selective formation of 2-trimethylsilyl-2-alkenenitriles. Among some Lewis acids, magnesium bromide gives the best E-selectivity in the formation of 2-trimethylsilyl-2-undecenenitrile. Stereospecific protodesilylation of 2-trimethylsilyl-2-alkenenitriles in an aqueous methanol solution of potassium fluoride accomplishes a new route to (Z)-2-alkenenitriles from aldehydes.Keywords
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